


Trick or Treat (A Wincest Halloween)

by callmeb, MothMeetsFlame



Series: Holidays with the Wincesters [14]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Crossdressing Dean, Daddy Kink, Dirty Talk, Edgeplay, Halloween, I don't know, M/M, Oral Sex, Parent/Child Incest, Riding, Sibling Incest, Spitroasting, Teasing, Underage Sex, and, cockslut!Dean, i forgot, i think, it's sexy, just saying, oh yeah, probably some other tags, schoolgirl!Dean, that's it for now
Language: English
Status: Completed
Published: 2014-11-01
Updated: 2014-11-01
Packaged: 2018-02-23 11:02:43
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,970
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2545202
Author URL: https://archiveofourown.org/users/callmeb/pseuds/callmeb, https://archiveofourown.org/users/MothMeetsFlame/pseuds/MothMeetsFlame
Summary: <blockquote class="userstuff">
              <p>Dean's a schoolgirl for Halloween. Sam and John are making it naughty.</p>
            </blockquote>





	Trick or Treat (A Wincest Halloween)

**Author's Note:**

> This, my friends, is the final installment of Holidays with the Wincesters. I know... sad to see it go *wipes away tear* But! There's still this lovely little fic to enjoy. And everyone give a big ol' thank-you kiss to my collab partner, [B](http://archiveofourown.org/users/callmeb/pseuds/callmeb). She's awesome, just saying. 
> 
> Enjoy ;)

Dean bit his lip and moaned. His pleated skirt flew out with every drop onto the thick cock inside of him, tickling his head while he rode his little brother.

Just these last few months, Sammy’s cock got huge, bigger than John’s even, and Dean couldn’t even deny how much he loved getting stretched open on it. If there was anyone who came even close to being the cockslut Sammy was, it was Dean.

He loved getting fucked open on John’s monster cock, but he always loved it more when Sammy was the one fucking himself back on their daddy’s rigid shaft, the cock disappearing inside of him while his little ass just swallowed it up. Sammy was all lithe muscles and whimpering pleas while he took it every way imaginable, and as much as Dean loved having their daddy’s cock in his ass, it didn’t even compare to watching his little brother ride him.

But then, his little brother wasn’t so little anymore. His cock grew, fucking thick and long and uncut, into a masterpiece. It became a compulsion trying to take his not-so-little brother into his throat, wanting to feel it thrust deep inside of him, to feel it split him open while he writhed beneath his little brother, payback for all the times he'd done the same to Sammy.

And Sammy loved to make his big brother ride him too, loved making Dean show how badly he wanted it, watching Dean put all his weight on Sam's lap, grinding, rutting, especially dressed as pretty as he was.

One look at Dean’s schoolgirl outfit—white Oxford shirt tucked into his plaid skirt, black stockings leading them to what Sam could only describe as the tallest hooker shoes he’d seen—and both him and John took hold of him to share him between them instead of trick-or-treating with the rest of the town.

Sam pulled Dean in roughly, and Dean practically fell on his little brother, straddling his hips while John fed the tip of his cock into Dean’s mouth.

Sam’s view was amazing, and he relished in having Dean ride him, mostly because his big brother whimpered pleas around their daddy’s cock while he did it, unable to make his muscles work well enough to fuck himself on Sammy’s rigid shaft like he wanted to. 

Dean moaned, the vibrations making John gasp and thrust deeper into Dean’s throat. Dean nearly gagged before he controlled himself and took his daddy deeper. He loved it when he lost control and fucked his throat, precome and spit making his mouth sloppy wet. But he also loved to be fucked hard and fast, to be held down and pounded into.

Sam enjoyed it, too. He loved watching Dean struggle to take his cock, loved how his eyes squeezed closed as he seated himself in his little brother’s lap, panting because Sammy’s cock was always hard to take no matter how much they prepped his little hole. And when Dean began the slow rise and fall to accustom himself to his brother’s size, his thighs trembled with the movement, and Sam knew that Dean wouldn’t be able to keep it up for long, that he’d need his little brother to fuck roughly into him.

The assault of his brother's cock against his prostate was too much for Dean to take, leaving it up to Sam to move, to grab Dean's hips and thrust into him from below, but not before he made his big brother beg for it.

Dean braced himself on Sam's chest, shaky but still whimpering with every twitch of the cock inside of him, trying to push himself back to take more. He tried not to beg, but Sam’s thrusts were too slow, too shallow, because Sammy wouldn’t give it to him completely until Dean begged for it.

Dean pulled the cock out of his mouth, much to John’s dismay, and pumped it loosely while he whined. "Please Sammy— _unh_ — Just fuck me. Sammy, please. I need it— _fuck_."

And Sammy couldn’t help but tease him. He slipped his hand under Dean’s skirt and thrust a finger into Dean's ass right next to his cock, not doing anything to give in to Dean's pleas, still keeping his thrusts shallow and teasing. He couldn’t help but gawk when his brother was like this, half fucked-out and whimpering with need.

"God, Dean, you really need it don't you? Need your little brother's cock, love how it feels inside you. How much do you want it, Dee? How bad do you want me to fuck you?"

Dean begged so pretty for his little brother. Back arching, hips trying to push Sammy's cock even deeper. John’s cock slipped out of Dean’s grip when he moved to stop boy's hips from taking Sam's cock fully inside him. "I think Sammy asked you a question, Dean."

"C'mon Sammy please just..." He cut himself off and bit his tongue. He wasn’t going to beg for it, could hold out a while longer before it came to that. He was sure of it.

John’s hands held tighter to Dean’s hips, not letting him move even an inch, though Dean was trying his hardest.

"No, Dean. Not until you answer your brother."

Dean shook his head no. He grinded his hips down harder trying to force more of his brother's thick cock inside of him, but John's hands held steady.

"Answer the question, Dean." Sammy smirked and continued teasing Dean’s hole, thrusting in so slowly that it could hardly be considered movement.

Dean moaned when the head of Sammy's cock rubbed against his prostate. The quick brush was all it took to tear down his will. "Fuck, yes, love it, Sammy, please. Need it. Want it all the time, so much. _Mmmm_ … Want you to fuck me so bad, Sammy, please."

" _Mmm_ , can't hear you loud enough, Dee. Say it again."

Dean moaned and held himself up over his brother, half out of his mind with a need he'd no doubt deny later. "Love it, Sammy. Fuck, love your cock. Want it in me all the time. Please, fuck, please more. God I need it so much, Sammy. More. Harder. Want it so bad."

"There's a good boy,” John praised. Wet lips touched themselves to the back of his neck for a moment. “Go on Sammy, give your big brother what he needs."

And Sammy may not have always done what he was told, but he had no intention of disobeying the order. He thrust deep into Dean's slick hole, making him keen. Dean collapsed onto Sam's chest, whimpering with every deep thrust. His cock leaked hard between them, the friction against Sam's stomach increasing with every piston of his hips.

He was so close to bursting that he couldn’t help but pant. His mouth moved to form words that wouldn’t make it past his lips. _So close, Sammy_ , he mouthed. _Please, more, please, more, pleasemoremoremoremore_.

And Sammy fucked in harder, faster. John held Dean's hips tight and made him meet every thrust, practically bouncing his boy up and down on Sammy’s cock.

" _Ohgodohgodfuckfucksammyplease_ "

"That's it Dean. Take it. Fuck, Dean, want you to come with me. Want you to come when I fill you up."

Dean whimpered and moaned into his brother's neck as his ass was pounded into.

John moaned from behind them. "Can you do that, baby boy?” he asked. “Can you come from your little brother's cock? C'mon, Dean. We know you love how stretched open you are."

"Fuck, Dean!" With Dean’s whimper, Sam came inside of him, stuffing him full of come that he promised to clean out of his brother's sloppy hole later. His cock pulsed while he fucked himself through his orgasm, and spurt after spurt shot inside of him.

Sam's muscles tensed, and his stomach once again brushed Dean's cock, this time keeping steady pressure as Dean impulsively writhed. Come shot into Dean’s skirt, coating the plaid with white tendrils of his release, and his back arched with the force of it. He collapsed against his little brother, come leaking through the fabric to soak Sam’s stomach, as both of them panted with exertion.

John soothed his hands down Dean's back and reached down between loose limbs to rub Sammy's tired sac. "Shhh boys. You did so good. But Daddy can't wait any longer. I think Dean deserves some more. What do you think? You want another fat cock in you?"

Both his boys whimpered as John lifted Dean's hips up again. Sammy's softening cock slid out, followed by a small trail of come. Dean hissed, but he still pushed back when John lined the head of his cock up with his sloppy hole.

Dean couldn’t move, couldn’t speak to tell his daddy that, yes, he craved his cock like he craved Sammy's, that he wanted it inside of him, filling him up with more come. Instead, he moaned, low and deep, and John knew just what he wanted.

"Don't worry, baby boy," John soothed. "I know what you want."

John pushed in until the head of his cock was nestled inside, and he moved as gentle as possible, Dean crying out in a mixture of pleasure and pain.

"Shhh. That's it. That's so good Dee. Let Daddy take you. I'll give you what you need, baby. Just want you to beg for me one last time. Beg for me and I’ll pound your sweet ass so good. You want that, don't you?"

But still, Dean could hardly speak. He groaned into Sammy's neck, arched his back to take more of his father.

"He wants it, Daddy. He wants it so damn bad."

Dean worked up the strength to nod his head, and that seemed to be good enough for John. He thrust in quickly, fucking his son with abandon, feeling how slick he is from the mix of spit, lube, and come. It fueled him to drive in deeper, drilling Dean's ass as his son involuntarily cried out, his over sensitive prostate completely abused.

Dean's fingers clawed at the bedding around Sam's shoulders. Small, whimpers and sobs tore from his throat as his ass was pounded. "Please" he rasped out in to his little brother's sweat-soaked skin.

And Sammy knew his brother's pleas like he knew his daddy's cock. He reached between them and thumbed over Dean’s head. His cock was flaccid between them, over-sensitive since he’d just come, but Sam knew that his brother loved it, loved being forced to take whatever they gave him.

Dean's hips twitched and he cried out, his brother's hand torturous on his cock while his daddy pounded into him from behind.

He begged again, voice wrecked and shaky, "Please, da-daddy. Sammy, please!"

His son's voice was thick and hoarse, and it had its desire effect. John pulled Dean roughly onto his cock and came with a shout inside of him.

Dean cried out as he was filled up again, so full. His ass clenched around John’s cock, and his body shook. Sam played with Dean’s shaft, rolling the empty sack with his fingers when Dean tried to pull away from him. It was so much, _too_ _much_. But it felt so good.

Sam wet his lips at the sight his brother made. His own cock was hard again, teenage hormones bringing him back up quickly. It was his favorite thing, to watch his brother pass out from being fucked over and over and over again, watching him walk gingerly the next day because he'd taken his little brother and his daddy into his ass so many times, practically fucking begged for it.

Sammy loved it even more knowing that he’d have no choice but to walk around like this when they went trick-or-treating later. Nothing said naughty schoolgirl like being stuffed with come. 

**Author's Note:**

> Aaaaaaaaaand that's all, folks. Let me know what you think :) And thanks-times-a-million to my friend, B. I hope everyone enjoyed the ride ;)


End file.
